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Winter Garden Homes For Sale & Real Estate - 820 homes

Winter Garden homes for sale are located in Orange County, Florida. Find homes in Winter Garden for sale with data from the Multiple Listing Service (MLS). Our REALTORS® can assist you in your real estate search for Winter Garden houses.

Location: Winter Garden

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  • 869 BENDING OAK TRL, WINTER GARDEN, FL 34787

    $520,000184 Days on yellowkey   MLS ID: O6358341

    REDUCED by $10,000 (1.9%) on 05/05/2026

    For Sale O6358341 - 869 BENDING OAK TRL, WINTER GARDEN, FL 34787 33 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1975
       Built: 2012
    Monthly Fee: $109
       Tax: $5,262 (2024)
    Community: Oaks/Brandy Lake 01 Rep A & B
    Single Family


    Estimated Monthly Payment: $3,397 (change assumption)
    Mortgage ($2,849) + Fees ($109) + Taxes in 2024 ($438)


    Taxes:$5,262

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 14255 HAMPSHIRE BAY CIR, WINTER GARDEN, FL 34787

    $1,300,00040 Days on yellowkey   MLS ID: O6395612

    For Sale O6395612 - 14255 HAMPSHIRE BAY CIR, WINTER GARDEN, FL 34787 73 photos

    Bed: 4   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 4625
       Built: 2003
    Monthly Fee: $141
       Tax: $12,364 (2025)
    Community: Bay Isle 48 17
    Single Family


    Estimated Monthly Payment: $8,294 (change assumption)
    Mortgage ($7,123) + Fees ($141) + Taxes in 2025 ($1,030)


    Taxes:$12,364

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 15043 PIGEON PLUM LN, WINTER GARDEN, FL 34787

    $594,00094 Days on yellowkey   MLS ID: S5143009

    For Sale S5143009 - 15043 PIGEON PLUM LN, WINTER GARDEN, FL 34787 23 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2695
       Built: 2016
    Monthly Fee: $241
       Tax: $8,470 (2024)
    Community: Summerlake Pd Ph 2C 2D 2E
    Single Family


    Estimated Monthly Payment: $4,202 (change assumption)
    Mortgage ($3,255) + Fees ($241) + Taxes in 2024 ($706)


    Taxes:$8,470

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 2154 OAKINGTON ST, WINTER GARDEN, FL 34787

    $469,90013 Days on yellowkey   MLS ID: O6402495

    For Sale O6402495 - 2154 OAKINGTON ST, WINTER GARDEN, FL 34787 39 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1585
       Built: 2002
    Monthly Fee: $243
       Tax: $5,166 (2025)
    Community: Stoneybrook West
    Single Family


    Estimated Monthly Payment: $3,248 (change assumption)
    Mortgage ($2,575) + Fees ($243) + Taxes in 2025 ($431)


    Taxes:$5,166

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 512 GARDEN HEIGHTS DR, WINTER GARDEN, FL 34787

    $564,900103 Days on yellowkey   MLS ID: S5142675

    REDUCED by $13,000 (2.2%) on 05/04/2026

    For Sale S5142675 - 512 GARDEN HEIGHTS DR, WINTER GARDEN, FL 34787 61 photos

    Bed: 4   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1700
       Built: 1974   Tax: $3,743 (2024)
    Community: Garden Heights
    Single Family


    Estimated Monthly Payment: $3,407 (change assumption)
    Mortgage ($3,095) + Taxes in 2024 ($312)


    Taxes:$3,743

    Elementary School: Dillard Street Elem

    High School: Ocoee High

    Tax Year: 2024

    Middle School: Lakeview Middle


  • 7107 BROWN PELICAN CT, WINTER GARDEN, FL 34787

    $625,00013 Days on yellowkey   MLS ID: O6400618

    0 Days Off yellowkey (back on 5/4/2026)

    For Sale O6400618 - 7107 BROWN PELICAN CT, WINTER GARDEN, FL 34787 35 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2751
       Built: 2017
    Monthly Fee: $252
       Tax: $6,112 (2025)
    Community: Summerlake Pd Phase 4A
    Single Family


    Estimated Monthly Payment: $4,186 (change assumption)
    Mortgage ($3,425) + Fees ($252) + Taxes in 2025 ($509)


    Taxes:$6,112

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 9433 EMERALD BERRY DR, WINTER GARDEN, FL 34787

    $729,80020 Days on yellowkey   MLS ID: O6401775

    0 Days Off yellowkey (back on 5/4/2026)

    For Sale O6401775 - 9433 EMERALD BERRY DR, WINTER GARDEN, FL 34787 62 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2063
       Built: 2024
    Monthly Fee: $99
       Tax: $8,457 (2025)
    Community: Summerlake Reserve
    Single Family


    Estimated Monthly Payment: $4,803 (change assumption)
    Mortgage ($3,999) + Fees ($99) + Taxes in 2025 ($705)


    Taxes:$8,457

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 10768 RHETT BUTLER ALY, WINTER GARDEN, FL 34787

    $426,00039 Days on yellowkey   MLS ID: O6396023

    INCREASED by $2,000 (0.5%) on 05/04/2026

    For Sale O6396023 - 10768 RHETT BUTLER ALY, WINTER GARDEN, FL 34787 48 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1636
       Built: 2023
    Monthly Fee: $268
       Tax: $5,866 (2025)
    Community: Storey Grove
    Townhouse


    Estimated Monthly Payment: $3,091 (change assumption)
    Mortgage ($2,334) + Fees ($268) + Taxes in 2025 ($489)


    Taxes:$5,866

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 13343 SUNNY RETREAT LN, WINTER GARDEN, FL 34787

    $849,00098 Days on yellowkey   MLS ID: O6379591

    REDUCED by $50,900 (5.7%) on 05/04/2026

    For Sale O6379591 - 13343 SUNNY RETREAT LN, WINTER GARDEN, FL 34787 49 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2214
       Built: 2023
    Monthly Fee: $544
       Tax: $10,256 (2024)
    Community: Del Webb Oasis
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,051 (change assumption)
    Mortgage ($4,652) + Fees ($544) + Taxes in 2024 ($855)


    Taxes:$10,256

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 16826 BROADWATER AVE, WINTER GARDEN, FL 34787

    $1,499,00070 Days on yellowkey   MLS ID: O6387379

    REDUCED by $41,000 (2.7%) on 05/04/2026

    For Sale O6387379 - 16826 BROADWATER AVE, WINTER GARDEN, FL 34787 58 photos

    Bed: 6   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 4451
       Built: 2019
    Monthly Fee: $218
       Tax: $9,892 (2025)
    Community: Waterside/Johns Lk-Ph 1
    Single Family


    Estimated Monthly Payment: $9,256 (change assumption)
    Mortgage ($8,213) + Fees ($218) + Taxes in 2025 ($824)


    Taxes:$9,892

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 14001 COUNTRY ESTATE DR, WINTER GARDEN, FL 34787

    $1,175,00014 Days on yellowkey   MLS ID: O6403044

    For Sale O6403044 - 14001 COUNTRY ESTATE DR, WINTER GARDEN, FL 34787 75 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3698
       Built: 1988
    Monthly Fee: $71
       Tax: $6,208 (2025)
    Community: Country Lakes
    Single Family


    Estimated Monthly Payment: $7,027 (change assumption)
    Mortgage ($6,438) + Fees ($71) + Taxes in 2025 ($517)


    Taxes:$6,208

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 1325 FETTLER WAY, WINTER GARDEN, FL 34787

    $279,90033 Days on yellowkey   MLS ID: O6393936

    REDUCED by $10,000 (3.4%) on 05/04/2026

    For Sale O6393936 - 1325 FETTLER WAY, WINTER GARDEN, FL 34787 38 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1440
       Built: 2004
    Monthly Fee: $61
       Tax: $3,653 (2025)
    Community: Westside Twnhms-Ph 05 A B & C
    Townhouse


    Estimated Monthly Payment: $1,899 (change assumption)
    Mortgage ($1,534) + Fees ($61) + Taxes in 2025 ($304)


    Taxes:$3,653

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 113 W DIVISION ST, WINTER GARDEN, FL 34787

    $549,99015 Days on yellowkey   MLS ID: S5148787

    For Sale S5148787 - 113 W DIVISION ST, WINTER GARDEN, FL 34787 24 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1487
       Built: 1951   Tax: $4,920 (2025)
    Community: Winter Garden Shores Rep
    Single Family


    Estimated Monthly Payment: $3,424 (change assumption)
    Mortgage ($3,014) + Taxes in 2025 ($410)


    Taxes:$4,920

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 9723 LOST CREEK DR, WINTER GARDEN, FL 34787

    $669,000184 Days on yellowkey   MLS ID: O6359309

    0 Days Off yellowkey (back on 5/4/2026)

    For Sale O6359309 - 9723 LOST CREEK DR, WINTER GARDEN, FL 34787 43 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2117
       Built: 2021
    Monthly Fee: $261
       Tax: $10,499 (2025)
    Community: Waterleigh
    Single Family


    Estimated Monthly Payment: $4,802 (change assumption)
    Mortgage ($3,666) + Fees ($261) + Taxes in 2025 ($875)


    Taxes:$10,499

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 7363 MEZZANO LN, WINTER GARDEN, FL 34787

    $469,999251 Days on yellowkey   MLS ID: O6340083

    REDUCED by $10,000 (2.1%) on 05/04/2026

    For Sale O6340083 - 7363 MEZZANO LN, WINTER GARDEN, FL 34787 25 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 1920
       Built: 2023
    Monthly Fee: $159
       Tax: $6,986 (2025)
    Community: Mezzano
    Townhouse


    Estimated Monthly Payment: $3,316 (change assumption)
    Mortgage ($2,575) + Fees ($159) + Taxes in 2025 ($582)


    Taxes:$6,986

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1408 SPRING RIDGE DR, WINTER GARDEN, FL 34787

    $459,00061 Days on yellowkey   MLS ID: O6390610

    2 Days Off yellowkey (back on 4/11/2026)

    For Sale O6390610 - 1408 SPRING RIDGE DR, WINTER GARDEN, FL 34787 25 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1614
       Built: 1991
    Monthly Fee: $25
       Tax: $1,722 (2025)
    Community: Crown Point Spgs
    Single Family


    Estimated Monthly Payment: $2,684 (change assumption)
    Mortgage ($2,515) + Fees ($25) + Taxes in 2025 ($144)


    Taxes:$1,722

    Elementary School: Dillard Street Elem

    High School: Ocoee High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 10693 PETRILLO WAY, WINTER GARDEN, FL 34787

    $799,00027 Days on yellowkey   MLS ID: O6399081

    2 Days Off yellowkey (back on 5/4/2026)

    For Sale O6399081 - 10693 PETRILLO WAY, WINTER GARDEN, FL 34787 60 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3149
       Built: 2021
    Monthly Fee: $102
       Tax: $8,845 (2025)
    Community: Winding Bay Ph 1B
    Single Family


    Estimated Monthly Payment: $5,217 (change assumption)
    Mortgage ($4,378) + Fees ($102) + Taxes in 2025 ($737)


    Taxes:$8,845

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 156 STANTON ESTATES CIR, WINTER GARDEN, FL 34787

    $1,200,00069 Days on yellowkey   MLS ID: O6384801

    For Sale O6384801 - 156 STANTON ESTATES CIR, WINTER GARDEN, FL 34787 64 photos

    Bed: 4   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3170
       Built: 2018
    Monthly Fee: $188
       Tax: $7,979 (2024)
    Community: Stanton Estates
    Single Family


    Estimated Monthly Payment: $7,428 (change assumption)
    Mortgage ($6,575) + Fees ($188) + Taxes in 2024 ($665)


    Taxes:$7,979

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2024

    Middle School: Lakeview Middle


  • 6560 CANDIED PEEL ALY, WINTER GARDEN, FL 34787

    $410,000553 Days on yellowkey   MLS ID: S5115131

    5 Days Off yellowkey (back on 5/4/2026)

    REDUCED by $20,000 (4.7%) on 04/27/2026

    For Sale S5115131 - 6560 CANDIED PEEL ALY, WINTER GARDEN, FL 34787 25 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 1902
       Built: 2018
    Monthly Fee: $400
       Tax: $5,843 (2023)
    Community: Hamlin Reserve
    Townhouse


    Estimated Monthly Payment: $3,133 (change assumption)
    Mortgage ($2,247) + Fees ($400) + Taxes in 2023 ($487)


    Taxes:$5,843

    Elementary School: None

    High School: None

    Tax Year: 2023

    Middle School: None


  • 3262 HANGING TIDE ST, WINTER GARDEN, FL 34787

    $750,000120 Days on yellowkey   MLS ID: S5141634

    For Sale S5141634 - 3262 HANGING TIDE ST, WINTER GARDEN, FL 34787 63 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3663
       Built: 2021
    Monthly Fee: $132
       Tax: $10,508 (2025)
    Community: Lakeview Preserve Ph 2
    Single Family


    Estimated Monthly Payment: $5,117 (change assumption)
    Mortgage ($4,109) + Fees ($132) + Taxes in 2025 ($876)


    Taxes:$10,508

    Elementary School: Lost Lake Elem

    High School: East Ridge High

    Tax Year: 2025

    Middle School: Windy Hill Middle




Why Bother Searching Elsewhere for Winter Garden Homes for Sale and Other Real Estate?

Winter Garden home, townhome, condo, villa, and other listing sales data is continuously updated on yellowkeyrealty.com. yellowkeyrealty.com offers one of the most exhaustive, current, and relevant set of data you can find on houses for sale in Winter Garden . You can use our website to view Multiple Listing Service (MLS) data on Winter Garden Real Estate. Feel free to reach out to a REALTOR ® at 1-954-369-1486 if you are unable to find specific information on any of our Winter Garden listings.



Data is updated at least once a week by Sunday nights. Some properties that appear for sale on this web site may subsequently have been sold and may no longer be available. The data relating to real estate for sale/lease on this web site come in part from a cooperative data exchange program of the multiple listing service (MLS) in which this real estate firm (Broker) participates. Data can be retrieved from any one of the following MLS’s: Greater Fort Lauderdale REALTORS®, Space Coast Association of REALTORS®, My Florida Regional MLS, Florida Gulf Coast MLS, "©2024 Northeast Florida Multiple Listing Service, Inc. All rights reserved." The properties displayed may not be all of the properties in the MLS’s database, or all of the properties listed with Brokers participating in the cooperative data exchange program. Properties listed by Brokers other than this Broker are marked with either the listing Broker’s logo or name or the MLS name or a logo provided by the MLS. Detailed information about such properties includes the name of the listing Brokers. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein, or for their use or interpretation by the user. The Florida Association of Realtors® and its cooperating MLSs do not create, control or review the property data displayed herein and take no responsibility for the content of such records. Federal law prohibits discrimination on the basis of race, color, religion, sex, handicap, familial status or national origin in the sale, rental or financing of housing.